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Two replaceable images within a <repeater>?

Hi all,

I'm trying to have two replaceable images within a repeater tag, however, the option to replace them is gone and i can change the image only via the description edit tool. Not only can I change just one image, but that image I uploaded is being duplicated into the second image I want to change. Thus so far, I've concluded that two replaceable images can't happen within a repeater? Any workaround to this?